Old Landing Winter Rentals & Holiday Homes

Discover winter rentals Old Landing - We found 1284 exact matches

About Old Landing Winter Rental on SunSkiResorts

Planning a winter vacation in Old Landing? Discover 1284 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Old Landing, DE perfect for your seasonal escape. Our listings include private vacation homes, cabins, condos, villas, resorts, and pet-friendly apartments. SunSki's winter vacation homes feature top amenities such as Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Winter accommodations in Old Landing start at US $463. The most popular properties in Old Landing include cabins, bungalows, and rental homes. Planning a snowboarding adventure? Explore our snowboard-friendly ski resorts, chalets, and cabins available for short-term or long-term stays. Whether it's a weekend getaway, monthly retreat, or an extended stay, SunSki ensures a memorable winter trip.

To book your winter vacation homes in Old Landing, visit SunSki's filter option, enter your travel dates, narrow down your preferences, and choose from our extensive list of rentals hassle-free. Explore our interactive map to uncover all accommodations in or around Old Landing and unlock incredible deals.

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Frequently Asked Questions About Old Landing Winter Rentals

There are a lot of options in Old Landing. If you plan on staying in the Old Landing area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Old Landing:

The average cost for winter rentals in Old Landing is $463 per night. SunSki has a wide list of great winter places to stay near Old Landing that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage/chalet rentals in Old Landing that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Old Landing on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Old Landing to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 1284 private swimming pools or indoor pools accommodations near Old Landing along with other great amenities.

About 1284 holiday rentals in Old Landing boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:

Yes, there are many luxury places to stay in Old Landing for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Old Landing with all the best amenities for your next trip.